1. Field of the Invention
The present invention relates to certain tetrazole derivatives that are useful as fungicides. More particularly, the present invention relates to a method for controlling fungi by contacting the fungi with a fungicidally effective amount of the tetrazole derivative compound, or by applying the tetrazole derivative compound to plant foliage or plant seed susceptible to attack by said fungi, or to a growth medium for the plant to be protected.
2. Description of Related Art
U.S. Pat. No. 3,865,570 discloses a method of regulating the growth of plants, which comprises applying to the plants a compound of the formula:
wherein Y is an aryl or heterocyclic group, optionally substituted, and X represents a hydrogen atom, a hydroxyalkyl group, a carboxylate ester group or a carboxyalkyl group, or a salt, ester, amide or nitrile thereof.
U.S. Pat. No. 5,869,504 discloses tetrazole derivatives of the formula
wherein R is a substituted or unsubstituted phenyl group, heterocyclic group, or benzo-fused heterocyclic group, which exhibit activity as insecticides and acaricides.
U.S. Pat. No. 6,020,355 discloses tetrazole derivatives of the formula
wherein R is a substituted or unsubstituted phenyl group, heterocyclic group, or benzo-fused heterocyclic group, which exhibit activity as insecticides and acaricides.
U.S. Pat. No. 6,297,275 discloses a method for controlling fungi using a phenylhydrazine derivative compound of the formula:
wherein: X is phenyl, phenylalkoxy, phenoxy, or benzyl, alone or in combination with one or more halogen, alkyl, or alkylthio; Y is hydrogen, alkanoyl, haloalkanoyl, or alkoxy carbonyl; and R is hydrogen, alkyl, haloalkyl, alkoxy, haloalkoxy, or phenylalkoxy.
U.S. Pat. No. 6,451,835 discloses fluoroethyl pyrazole compounds of the formula:
wherein X and Y are independently selected from the group consisting of hydrogen, halogen, alkyl, haloalkyl, nitro, alkylthio, alkylsulfinyl, alkylsulfonyl, and haloalkoxy. These compounds are useful as insecticides, nematicides, fungicides, and acaricides.
U.S. Patent Application Publication No. 2004/0266738 discloses certain phenoxyphenylhydrazine derivatives that are useful as fungicides.
U.K. Patent No. 1,353,699 discloses a method of regulating the growth of plants, which comprises applying for uptake by the plants a compound of the formula:
wherein Y is an aryl or heterocyclic group, optionally substituted, and X represents a hydrogen atom, a carboxylate ester group, a hydroxyalkyl group or a carboxyalkyl group, or a salt, ester amide or nitrile thereof.
U.K. Patent No. 1,381,840 is directed to tetrazole compounds useful in the method of U.K. Patent No. 1,353,699.
Buzilova, S. R. et al. (Journal of Organic Chemistry of USSR, pp. 1375-1379(1989)) disclose the synthesis of 1(2)-cyanoalkyltetrazoles by the alkylation of 5-substituted tetrazoles with chloroacetonitrile in dioxane in the presence of potassium hydroxide and triethylbenzylammonium chloride. 5-Cyanoalkyltetrazoles were synthesized as a result of the substitution of chlorine in 5-chloroalkyltetrazoles by a cyano group in the presence of dibenzo-18-crown-6 ether.
Janda, L. et al. (Chem. Papers 43:63-71 (1989)) disclose the preparation of a mixture of ethyl 5-(5-bromo-2-furyl)-1-tetrazolylacetate and ethyl 5-(5-bromo-2-furyl)-2-tetrazolylacetate by the alkylation of 5-(5-bromo-2-furyl)-1H-tetrazole with ethyl bromoacetate. The two products of the mixture were chromatographically separated and the ester substituted in position 1 was the substrate for the nucleophilic substitution with 4-substituted thiophenols. The resulting ethyl 5-[5-(4-R-phenylthio-2-furyl)-1-tetrazolylacetates were hydrolyzed to the corresponding acids.
Brekhov, Y. V. et al. (Journal of Organic Chemistry of USSR, pp 1539-1542 (1993)) disclose a series of derivatives of C- and N-substituted cyanomethyltetrazoles that were brought into alkylation, condensation, addition to multiple bonds, dimerization, and azo coupling reactions. The chemical reactivity of the methylene fragment is said to increase in the series of 5-, 1-, and 2-cyanomethyltetrazoles.
Verkhozina, O. N. et al. (Russian Journal of Organic Chemistry 39(12), pp 1792-1796 (2003)) disclose the synthesis of polynuclear blocks consisting of nonfused heterocycles of the azole series, connected through methylene bridges, by successive addition of azole units via cycloaddition of organic azides to the triple bond of N-(2-propynyl)azoles, as well as via reaction of azide ion at the cyano group of cyanomethylazoles. Initial N-(2-propynyl)azoles were prepared by reaction of 2-propynyl bromide with 1,2,3-triazoles, benzotriazole. and tetrazoles; cyanomethylazoles were obtained by alkylation of azoles with chloroacetonitrile. An analogous scheme was used to add heterocyclic units to 2-phenyl-1,2,3-triazole-4-carbonitrile. In this case, the first two heterocyclic units are linked through the ring carbon atom.
The disclosures of the foregoing are incorporated herein by reference in their entirety.